Cosmetic composition, compound and cosmetic treatment method

ABSTRACT

The invention relates to a cosmetic composition, particularly for hair care, and to a method for cosmetically treating keratin material, particularly the hair, using the compounds of Formula (I), where: —n=1, 2, 3, or 4; —R1, R′1, R2, and R′2 are H, —OH, —NRR′, or a C1-C18 carbon group capable of containing one or more heteroatoms selected from among O, S, and N; and —Z is a multivalent carbon radical optionally substitutable and/or interruptible by specific groupings, it being understood that said radical Z includes at least one heteroatom selected from among N, O, and S.

The present invention relates to a method for cosmetic treatment ofkeratin materials, in particular the hair, using a compositioncomprising compounds capable of forming hydrogen bonds, and also to thecosmetic compositions thus prepared.

In the cosmetics industry, there is a constant desire to improve theproperties of keratin materials and to combat damage, such as externalattacks, for instance pollution and ultraviolet radiation, or chemicalattacks, for instance those caused by dyeing or permanent-wavingtreatments.

Among the damage suffered by the hair, mention may in particular be madeof a loss of sheen, an increased hydrophilic nature, a loss ordetachment of some of the scales, and difficulties in disentangling.

In order to improve the properties of the hair, it is known practice touse compositions containing cosmetic active agents in order to providethe keratin materials, such as the hair, with all the beneficial effectsassociated with these cosmetic active agents. However, the persistenceand therefore the effectiveness of these active agents are notsufficient, since they can be easily removed with shampoo, oralternatively they do not form a homogeneous deposit at the surface ofthe hair.

The object of the present invention is to propose a cosmetic compositionwhich can be used for cosmetically treating the hair, and can give thehair long-lasting cosmetic properties.

It has in fact been noted that compounds comprising entities capable offorming physical interactions with one another can give the hairadvantageous cosmetic qualities. These compounds are in particularcharacterized by the presence of at least one entity capable of givingat least 3 hydrogen bonds, in particular 4 hydrogen bonds, and also bytheir low mass.

The subject of the present invention is therefore a method forcosmetically treating keratin materials, which comprises applying tosaid keratin materials a cosmetic composition comprising a compound offormula (I):

in which:

-   n=1, 2, 3 or 4;-   R1, R′1, R2 and R′2, which may be identical or different, represent    H, —OH, —NRR′ (with R and R′, which may be identical or different,    being H or a linear or branched C1-C12 alkyl radical); or a linear,    branched and/or cyclic, saturated or unsaturated, optionally    aromatic, C1-C18 carbon-based, in particular alkyl, group which can    contain one or more heteroatoms chosen from O, S and N;-   p and q are, independently of one another, integers between 1 and    16;-   X and X′ are, independently of one another, chosen from —O— and    —NH—.-   Z represents a multivalent radical chosen from:-   (i) a linear or branched, saturated or unsaturated, C1 to C32    carbon-based, in particular hydrocarbon-based, radical, optionally    interrupted or substituted, one or more times, with an optionally    aromatic C3-C12 (hetero)cycle; or-   (ii) an optionally aromatic C3-C12 (hetero)cyclic carbon-based, in    particular hydrocarbon-based, radical, optionally substituted with    one or more linear or branched, saturated or unsaturated, C1 to C32    carbon-based, in particular hydrocarbon-based, radicals;    it being possible for said Z radical to be:-   substituted with 1 to 12 groups chosen from —OH, —SO₃R, —OSO₃R,    —SO₃H, —OSO₃H, —COOH, —COOR, —CONRR′ and —N⁺RR′R″, with R, R′ and    R″═C1-C12 alkyl, in particular methyl; and/or-   interrupted with 1 to 12 groups chosen from:    -   (i) the following divalent groups: —S—, —NH— (or ═NH), —O—,        —C(O)—, —SO₂—,

with R′ and R″, which may be identical or different, representing ahydrogen atom or a linear, branched and/or cyclic, saturated orunsaturated, carbon-based, in particular alkyl, radical containing 1 to22 carbon atoms, (i) optionally substituted with one or more groupschosen from —SO₃R₁, —OSO₃R₁, —COOR₁, —Si(OR₁)₃, —N⁺R₁R₂R₃ or —NR₁R₂, inwhich R₁, R₂ and R₃, independently of one another, are chosen from H andC1-C22, in particular C1-C12, alkyl, preferably methyl; and/or (ii)optionally interrupted with one or more groups chosen from —NH, —O— and—C(O)— (alone or in combination);

-   -   (ii) the following trivalent groups:

R′ being as defined above for the divalent groups, said trivalent groupsbeing generally present at the junction of said radicals (in particularwhen Z is trivalent);it being understood that said Z radical bears at least one substitutiongroup chosen from: —OH, —COOH, —COOR (in particular COOMe), CONRR′ and—N⁺RR′R″; and/or at least one interruption group chosen from: —S—, —NH—(or ═NH),

Another subject of the invention is a cosmetic composition comprising,in a cosmetically acceptable medium, at least one such compound offormula (I).

The compounds of formula (I) constitute yet another subject of theinvention.

It has been noted that depositing a compound according to the inventiononto the hair or causing a compound according to the invention topenetrate into the hair makes it possible to provide the hair with abeneficial effect. Without being bound by the present explanation, it ispossible to imagine that ureidopyrimidone entities are capable ofgenerating, in situ in or on the hair, a crosslinked network by physicalassociations between molecules. When deposited on the hair or the skin,said compound becomes involved in and trapped in a crosslinked deposit,which increases its remanence, in particular with respect to sebum,water and shampoo. Moreover, since the crosslinking is a physicalcrosslinking, it is possible for the effect to be persistent while atthe same time allowing the compound to be removed during make-upremoval. The removal of the deposit can in particular consist of rinsingwith a cleansing composition applied at ambient temperature or at ahigher temperature, or using a make-up remover, or by using any knownagent for breaking hydrogen bonds.

The present invention can in particular make it possible to hydrate andreinforce keratin materials, and to provide long-lasting softness andsheen, such that the effect remains perceptible after at least oneshampooing operation.

The term “reinforcement of keratin materials” is intended to mean inparticular an improvement in the mechanical properties, which may resultin:

-   an increase in their rigidity, which gives them greater strength and    body; or else-   a decrease in their deformation, in particular under wet conditions,    which allows the hair to readily return to its initial shape once    dried, and results in an improvement in the dynamics of the hair; or    else-   better resistance to tensile mechanical forces which are applied    thereto, for example during combing, and which can lead to breaking    of the hair.

Moreover, to be able to treat the hair in situ can also make it possibleto bring protective and repair properties to the hair, following adyeing, bleaching, permanent-waving, smoothing or hair straighteningtreatment.

Creating this crosslinked network in the hair also makes it possible toavoid premature bleeding of a dye.

The compounds according to the invention can therefore both coat thehair, and therefore provide in particular reinforcement properties, andalso penetrate into the hair and provide, in situ, protection or repairproperties, in particular.

Many compounds which incorporate ureidopyrimidone (UPY) units have beendescribed in the literature and studied for their self-assemblingproperty by fundamental research laboratories. However, none of thesedocuments describes the application of these compounds to keratinmaterials, nor even the possible use thereof for reinforcing saidmaterials.

In the cosmetics field, mention may be made of WO 02098377 whichdescribes, in general, compounds comprising UPY units for cosmeticapplications to the skin and the hair. Mention may also be made of WO2003032929, which describes the preparation of supramolecular polymersand the use thereof in hair applications. Mention may also be made of WO2004016598, which describes the preparation of supramolecular polymersand the use thereof in varied applications, including cosmeticapplications. Alternatively, mention may be made of WO 2005042641, whichdescribes the preparation of supramolecular polymers, in particular ofpolyurethane type, and the use thereof in varied applications, includingcosmetic applications.

In all these documents, the compounds described are polymers, andtherefore high-molecular-weight compounds, which will not thereforepenetrate into the hair in order to provide it with beneficialproperties, in particular in terms of protection of the hair.

The compound which can be used in the context of the invention thereforecorresponds to formula (I):

in which:

-   n=1, 2, 3 or 4; preferably n=1 or n=2;-   R1, R′1, R2 and R′2, which may be identical or different, represent    H, —OH, —NRR′ (with R and R′, which may be identical or different,    being H or a linear or branched C1-C12, preferably C1-C4, alkyl    radical, and better still a methyl or ethyl radical); or a linear,    branched and/or cyclic, saturated or unsaturated, optionally    aromatic, C1-C18, preferably C1-C12, carbon-based, in particular    alkyl, group which can contain one or more heteroatoms chosen from    O, S and N; these heteroatoms can in particular be present in the    form of an OH, COOH and/or NRR′ radical.

The R1, R2, R′1 and R′2 radicals can in particular be chosen from:

-   H;-   NH₂;-   a C1-C18 alkyl group, optionally substituted or interrupted with a    quaternary ammonium radical, and/or optionally substituted with one    or more amino (NH₂), ester (COOH) and/or hydroxyl (OH) functions;-   a C4-C12 cycloalkyl group, optionally substituted with one or more    amino (NH₂), ester (COOH) and/or hydroxyl (OH) functions;-   a C4-C12 aryl group, optionally substituted with one or more amino    (NH₂), ester (COOH) and/or hydroxyl (OH) functions; and/or    optionally substituted with one or more PEG groups of formula    —(CH₂CH₂O)_(m)— with m=2 to 15;-   a C1-C4 alkoxy group;-   an aryl(C1-C4)alkoxy group, optionally substituted with one or more    amino (NH₂), ester (COOH) and/or hydroxyl (OH) functions.

Preferably, R1 and/or R′1 represent(s) H.

Preferably, R2 and/or R′2 represent(s) H, CH₃, C₇H₁₅, C₁₃H₂₇ or aryl,preferably methyl;

-   p and q are, independently of one another, integers between 1 and    16, in particular between 2 and 12, or even between 3 and 8, and in    particular 6;-   X and X′ are, independently of one another, chosen from —O— and    —NH—; preferably X═X′; and even better still X═X′═O; and-   Z represents a multivalent radical (divalent to pentavalent,    according to the value of n), chosen from:-   (i) a linear or branched, saturated or unsaturated, C1 to C32    carbon-based, in particular hydrocarbon-based (in particular alkyl)    radical, optionally interrupted or substituted, one or more times,    with an optionally aromatic C3-C12 (hetero)cycle; or-   (ii) an optionally aromatic, C3-C12 (hetero)cyclic carbon-based, in    particular hydrocarbon-based (in particular alkyl), radical,    optionally substituted with one or more linear or branched,    saturated or unsaturated, C1 to C32 carbon-based, in particular    hydrocarbon-based, radicals;    it being possible for said radical to optionally be:-   substituted with 1 to 12 groups chosen from —OH, —SO₃R, —OSO₃R,    —SO₃H, —OSO₃H, —COOH, —COOR (in particular COOMe), —CONRR′ and    —N⁺RR′R″, with R, R′ and R″═C1-C12 alkyl, in particular methyl;    and/or-   interrupted with 1 to 12, in particular 1 to 8, or even 1 to 6,    groups chosen from:    -   (i) the following divalent groups: —S—, —NH— (or ═NH), —O—,        —C(O)—, —SO₂—,

with R′ and R″, which may be identical or different, representing ahydrogen atom or a linear, branched and/or cyclic, saturated orunsaturated, carbon-based, in particular alkyl, radical containing 1 to22 carbon atoms, (i) optionally substituted with one or more groupschosen from —SO₃R₁, —OSO₃R₁, —COOR₁, —Si(OR₁)₃, —N⁺R₁R₂R₃ or —NR₁R₂, inwhich R₁, R₂ and R₃, independently of one another, are chosen from H andC1-C22, in particular C1-C12, alkyl, preferably methyl; and/or (ii)optionally interrupted with one or more groups chosen from —NH—, —O— and—C(O)— (alone or in combination):

-   -   (ii) the following trivalent groups:

R′ being as defined above for the divalent groups, said trivalent groupsbeing generally present at the junction of said radicals (in particularwhen Z is trivalent);it being understood that said Z radical bears at least one substitutiongroup chosen from: —OH, —COOH, —COOR (in particular COOMe), CONRR′ and—N⁺RR′R″; and/or at least one interruption group chosen from: —S—, —NH—(or ═NH),

The Z radical may preferably be a saturated, linear or branched, alkylradical containing 1 to 32, in particular 2 to 18, or even 3 to 12,carbon atoms, it being understood that it comprises at least onesubstitution/interruption group as defined above.

Preferably, said substitution group is chosen from —COOH, —COOMe or—CONRR′ (with R and R′═C1-C6 alkyl, in particular methyl).

Preferably, said interruption group is chosen from —NH—, —N⁺(R′)(R″)—and N (trivalent).

In particular, the groups may be present in the form of a combinationsuch as, for example, —C(O)O—, —OC(O)O—, —NR′C(O)—, —NR′C(O)NR″—,—NR′C(O)O—, —NRSO₂— or —NR—SO₂—NR′—, or even in the form —(CH₂CH₂O)_(x)—with x=2 to 15.

Preferably, R′ and R″ represent a C1-C12 alkyl radical, in particular amethyl or ethyl radical.

The compounds of formula (I) may correspond most particularly to thefollowing structure (R1═R′1=H):

and even better still to the structures hereinafter:

or even:

in which Z, p and q, and n are as defined above, with preferably n=1 or2.

Preferably, the Z radical represents a linear or branched, saturated orunsaturated, divalent or trivalent C1 to C32 hydrocarbon-based radicalcomprising at least one unit of the type —NR′—, —N⁺R′R″—, —S—,—NR′C(O)—, —NR′C(O)NR″— or —NR′C(O)O— with R′ and R″ chosen fromhydrogen, or a C3-C7 cycloalkyl, benzyl, phenyl or linear or branchedC1-C22 alkyl chain.

Most particularly, when n=1, the divalent Z radical can be chosen from:

and most particularly divalent Z can be:

with p=1 to 6, in particular 2 or 3.

When n=2, the trivalent Z radical can be chosen from:

with p=1 to 6, in particular 2 or 3.

Preferably the compounds of the formula (I) can be chosen from thefollowing compounds:

Preferably, the weight-average molecular weight (Mw) of the compoundaccording to the invention is less than or equal to 1200 g/mol. This lowmolecular weight promotes in particular the penetration of the compoundsinto the hair.

The compounds of formula (I) can be prepared according to any of theknown methods.

If the following group is referred to as A:

and the following group is referred to as W:

the compounds according to the invention can therefore be representedschematically in the following way: A-W-(A)_(n).

They can be obtained during reaction:

-   between a reactive function bonded to the group A and a reactive    function borne by the group W; or else-   between a reactive function bonded to a precursor of the group A and    a reactive function borne by the group W so as to simultaneously    form the group A and the entity A-W;    the two reactive functions being, of course, capable of reacting    with one another and it being possible for them to be bonded    directly or via a divalent segment to the group A and/or to the    group Z and/or to the precursor of said group A.

The reactive functions can preferably be chosen from the followingfunctions:

-   isocyanate —N═C═O;-   isothiocyanate —N═C═S;-   carboxylic acid or ester —COOR_(a) or activated ester COOR_(b) with    R_(a) being H or a linear or branched, C₁-C₁₂, preferably C₁-C₄    alkyl radical, and better still a methyl or ethyl radical; and    OR_(b) being chosen from phenoxy, 4-nitrophenoxy,    2,4,5-trichlorophenoxy and the following radicals:

-   acyl halide,-   acyl imidazole or acyl benzotriazole of formula:

-   acid anhydride,-   activated carbamic acid —NHCOX with X═Cl, imidazole, or OR_(b) as    defined above;-   hydroxyl (OH) or activated hydroxyl, for example in O-tosylate form,-   primary or secondary amine —N(R_(a))₂, with R_(a), which may be    identical or different, being as defined above;-   a function chosen from:

with R_(a), which may be identical or different, being as defined above.

Preferably, the reactive functions that are a precursor of the bondbetween W and A are chosen from isocyanate, amine or hydroxyl functionsor functions of the formula:

A particular method for obtaining A-W- is the one described in thearticle by Katritzky et al., Comprehensive Organic Functional GroupTransformations, Pergamon: Oxford, 1995, vol. 6, pp. 500-506 or else inArkiv der Pharmazie, 314(1), 34-41, 1981.

It is in particular possible to react:

-   an isocytosine B with an activated carbamic acid:

-   an isocytosine B with an amine-derived isocyanate:

-   an isocytosine comprising an activated carbamic function C, with an    amine:

-   a β-keto ester D with a guanylalkylurea derivative E:

Another method for preparing A-W- consists in synthesizing a compound ofthe following type:

and then reacting it with an alcohol or an amine.

The divalent group R′1 represents, for example, a group chosen from:1,2-ethylene, 1,6-hexylene, 1,4-butylene, 1,6-(2,4,4-trimethylhexylene);1,4-(4-methylpentylene), 1,5-(5-methylhexylene),1,6-(6-methylheptylene); 1,5-(2,2,5-trimethylhexylene),1,7-(3,7-dimethyloctylene); isophorone; 4,4′-methylene-biscyclohexylene,tolylene, 2-methyl-1,3-phenylene; 4-methyl-1,3-phenylene;4,4-biphenylenemethylene; and preferably isophorone; —(CH₂)₂—; —(CH₂)₆—;—CH₂CH(CH₃)—CH₂—C(CH₃)₂—CH₂—CH₂; 4,4′-methylenebiscyclohexylene;2-methyl-1,3-phenylene. Preferably, R′1=isophorone or 1,6-hexylene.

Particularly preferably, the compounds of formula (I) are soluble ordispersible in water or soluble in water basified using a 28% aqueousammonia solution (the pH of the solution is then between 8 and 10).

The term “soluble” is intended to mean that the compound forms a clearsolution, at a concentration of 1% by weight in the medium, at 25° C.and 1 atm.

The term “dispersible” is intended to mean that the compound forms inthe medium, at a concentration of 1% by weight at 25° C. and 1 atm, astable suspension or dispersion of fine particles, which are generallyspherical. The term “stable” is intended to mean that the suspensiondoes not precipitate and does not therefore display any visible deposit.The average size of the particles constituting the suspension or thedispersion is preferably less than 1 μm, and more generally rangesbetween 5 and 400 nm, preferably 10 to 250 nm. These particle sizes aremeasured by any conventional light scattering method.

The compounds according to the invention find a most particularapplication in the cosmetics field, in particular in the hair-relatedfield.

The amount of compound present in the cosmetic compositions of theinvention depends, of course, on the type of composition and on thedesired properties, and can vary within a very wide range, generallybetween 0.001% and 15% by weight, preferably between 0.005% and 10% byweight, in particular between 0.01% and 8% by weight, or even between0.1% and 7% by weight, relative to the total weight of the composition.

The cosmetic compositions can of course comprise a mixture of compoundsof formula (I).

The compositions according to the invention may be in any of thegalenical forms conventionally used, and in particular in the form of anaqueous, alcoholic or aqueous-alcoholic, or oily solution or suspension;a solution or a dispersion of the lotion or serum type, an emulsion, inparticular of liquid or semi-liquid consistency, of the O/W, W/O ormultiple type; a suspension or emulsion of soft consistency of creamtype (O/W) or (W/O); an aqueous or anhydrous gel, or any other cosmeticform. Preferably, the composition is in the form of an aqueoussuspension, serum or lotion.

These compositions can be packaged, in particular in pump dispensers orin aerosol containers, in order to apply the composition in vaporizedform (lacquer) or in the form of a mousse. Such packaging forms areindicated, for example, when it is desired to obtain a spray or amousse, for treating the hair. In these cases, the compositionpreferably comprises at least one propellant.

The compositions according to the invention comprise a cosmeticallyacceptable medium, i.e. a medium which is compatible with keratinmaterials, in particular the skin of the face or of the body, the lips,the hair, the eyelashes, the eyebrows and the nails.

Said medium preferably comprises at least one customary cosmeticingredient, in particular chosen from propellants; water, carbon-basedoils; silicone oils; C8-C40 alcohols, C8-C40 esters, C8-C40 acids; C1-C7alcohols, ketones, organic solvents, nonionic surfactants, cationicsurfactants, anionic surfactants, amphoteric surfactants, zwitterionicsurfactants; sunscreens; moisturizers; antidandruff agents;antioxidants; reducing agents; oxidation bases, couplers, oxidizingagents, direct dyes; hair-straightening agents, pearlescent andopacifying agents; plasticizers or coalescence agents; hydroxy acids;pigments; fillers; silicones; thickeners; emulsifiers; polymers; urea,and agents for producing a basic pH. Said medium can of course compriseseveral cosmetic ingredients appearing in the list above.

Depending on their nature and the purpose of the composition, thecustomary cosmetic ingredients can be present in normal amounts, whichcan be readily determined by those skilled in the art, and which can,for each ingredient, be from 0.01% to 80% by weight.

The composition can in particular comprise water, one or more C1-C7alcohols, alone or as a mixture with water, and in particular awater/ethanol, water/isopropanol or water/benzyl alcohol mixture.

The carbon-based, in particular hydrocarbon-based, oils and/or thesilicone oils can be present in a proportion of from 0.01% to 20% byweight, in particular 0.02% to 10% by weight, relative to the totalweight of the composition. Mention may in particular be made ofhydrogenated or nonhydrogenated plant, animal or mineral oils, saturatedor unsaturated, linear or branched, cyclic or aliphatic,hydrocarbon-based synthetic oils, for instance poly(alpha-olefin)s, inparticular polydecenes and polyisobutenes; water-soluble orwater-insoluble, organomodified or nonorganomodified, volatile ornonvolatile silicone oils; fluoro or perfluoro oils; mixtures thereof.

The alcohols, the esters and the acids, having 8 to 40 carbon atoms, canbe present in a proportion of from 0.01% to 50% by weight, in particular0.1% to 20% by weight, relative to the total weight of the composition.

Mention may in particular be made of C12-C32, in particular C12-C26,linear-chain or branched-chain fatty alcohols, and in particular cetylalcohol, stearyl alcohol, cetylstearyl alcohol, isostearyl alcohol,octyldodecanol, 2-butyloctanol, 2-hexyldecanol, 2-undecylpentadecanol,oleyl alcohol or linoleyl alcohol.

Mention may also be made of alkoxylated, in particular ethoxylated,C8-C40, in particular C16-C20, fatty alcohols, preferably comprisingfrom 10 to 50 mol of ethylene oxide and/or of propylene oxide, such asoleth-12, ceteareth-12 and ceteareth-20, oxypropylenated stearylalcohol, in particular comprising 15 mol of propylene oxide,oxyethylenated lauryl alcohol, in particular comprising more than 7oxyethylenated groups, and also mixtures thereof.

Mention may also be made of C16-C40 linear-chain or branched-chain fattyacids, and in particular 18-methyleicosanoic acid, coconut oil orhydrogenated coconut oil acids; stearic acid, lauric acid, palmitic acidand oleic acid, behenic acid, and mixtures thereof.

Mention may also be made of C16-C40 linear-chain or branched-chain fattyesters, such as esters of polyols derived from fatty acids containingfrom 8 to 30 carbon atoms, and the oxyalkylenated, and in particularoxyethylenated, derivatives thereof, the polyols preferably being chosenfrom sugars, C2-C6 alkylene glycols, glycerol, polyglycerols, sorbitol,sorbitan, polyethylene glycols, polypropylene glycols, and mixturesthereof.

The nonionic, cationic, anionic, amphoteric or zwitterionic surfactants,and also mixtures thereof, can be present in a proportion of from 0.01%to 50% by weight, in particular 0.05% to 40% by weight, or even 0.1% to30% by weight, relative to the total weight of the composition.

The propellants can be present in a proportion of from 5% to 90% byweight, relative to the total weight of the composition, and moreparticularly in a proportion of from 10% to 60% by weight.

The suncreens can be present in a proportion of from 0.01% to 20% byweight, in particular 0.5% to 10% by weight, relative to the totalweight of the composition.

The moisturizers can be present in a proportion of from 0.01% to 20% byweight, in particular 0.1% to 7% by weight, relative to the total weightof the composition.

The antidandruff agents can be present in a proportion of from 0.001% to20% by weight, in particular 0.01% to 10% by weight, relative to thetotal weight of the composition, preferably 0.1% to 5% by weight.

The antioxidants can be present in a proportion of from 0.05% to 1.5% byweight, relative to the total weight of the composition.

The reducing agents can be present in a proportion of from 0.1% to 30%by weight, in particular 0.5% to 20% by weight, relative to the totalweight of the composition.

The oxidation bases can be present in an amount of between 0.001% and10% by weight, preferably from 0.005% to 6% by weight, relative to thetotal weight of the composition.

The couplers can be present in an amount of between 0.001% and 10% byweight, preferably from 0.005% to 6% by weight, relative to the totalweight of the composition.

The oxidizing agents can be present in an amount of between 1% and 40%by weight, preferably between 1% and 20% by weight, relative to theweight of the composition.

The direct dyes can be present in an amount of between 0.001% and 20% byweight, preferably from 0.01% to 10% by weight, relative to the totalweight of the composition.

The hair-straightening agents can be present in a proportion of from0.01% to 3.5% by weight, in particular 0.05% to 1.5% by weight, relativeto the total weight of the composition.

The pearlescent and opacifying agents can be present in a proportion offrom 0.01% to 3% by weight, in particular 0.05% to 2.5% by weight,relative to the total weight of the composition.

The plasticizers or coalescence agents can be present in a proportion offrom 0.1% to 25% by weight, in particular 1% to 10% by weight, relativeto the total weight of the composition.

The hydroxy acids can be present in a proportion of from 1% to 10% byweight, in particular 2% to 5% by weight, relative to the total weightof the composition.

The pigments and fillers can be present in a proportion of from 0.01% to50% by weight, in particular 0.02% to 30% by weight, relative to thetotal weight of the composition.

The silicones may be volatile or nonvolatile; mention may in particularbe made of modified or unmodified polyorganosiloxanes, i.e.polyorganosiloxane oils, gums and resins, as they are or in the form ofsolutions in organic solvents, or in the form of emulsions ormicroemulsions. They can be present in an amount of from 0.01% to 40% byweight, in particular 0.05% to 20% by weight, relative to the totalweight of the composition.

The thickeners can be present in a proportion of from 0.01% to 10% byweight, in particular from 0.1% to 5% by weight, relative to the totalweight of the composition.

The polymers, which are in particular water-soluble or soluble incarbon-based and/or silicone oils, can be present in a proportion offrom 0.01% to 20% by weight, in particular 0.1% to 10% by weight,relative to the total weight of the composition.

Among the agents for producing a basic pH, mention may be made ofaqueous ammonia and also the bases commonly used in the cosmeticsindustry.

Those skilled in the art will take care to select the ingredients whichare part of the composition, and also the amounts thereof, in such a waythat they are not detrimental to the properties of the compositions ofthe present invention.

The cosmetic composition according to the invention may be in the formof a care, cleansing and/or makeup product for the skin of the body orthe face, the lips, the eyebrows, the eyelashes, the nails and the hair,a suntan or self-tanning product, a body hygiene product, a hairproduct, in particular a hair care, cleansing, styling, shaping ordyeing product.

It is especially of particularly advantageous use in the hair-relatedfield, in particular for hairstyle retention or hair shaping, or caringfor, cosmetically treating or cleansing the hair. The hair compositionsare preferably shampoos, conditioners, styling or care gels, carelotions or creams, conditioning agents, hairsetting lotions, blow-dryinglotions, setting and styling compositions, such as lacquers or sprays;hair restructuring lotions; lotions or gels for combating hair loss,antiparasitic shampoos, antidandruff lotions or shampoos, or shampoosfor treating seborrhoea. It can in particular be in the form of a hairdyeing product, in particular an oxidation dyeing product, optionally inthe form of a dye shampoo; in the form of a permanent-waving,hair-straightening or bleaching composition, or else in the form of arinse-out or leave-in composition, to be applied before or after dyeing,bleaching, permanent-waving or hair-straightening, or else between thetwo steps of a permanent-waving or hair-straightening operation.

The composition according to the invention may also be in the form of acare, in particular moisturizing, composition for the skin of the bodyor of the face, the lips and/or the skin appendages, in particular acare product for use in cosmetically treating the skin, and inparticular in moisturizing it, smoothing it, depigmenting it, nourishingit, and protecting it against sunlight, or conferring on it a specificcosmetic treatment. Thus, it may be a lip care base, a fixing base forlipsticks, an antisun or artificial tanning composition, a (day, night,antiageing, moisturizing) care composition for the face; a mattifyingcomposition; a composition for cleansing the skin, for example amakeup-removing product or a bath or shower gel, or a cleansing bar orsoap; a body hygiene composition, in particular a deodorant orantiperspirant product, or else a depilatory composition, or anaftershave gel or lotion. It may also be in the form of a makeup productfor the skin of the body or of the face, the lips, the eyelashes, thenails or the hair; in particular a foundation, a blusher, a face powder,an eyeshadow, a concealer, an eyeliner, a mascara, a lipstick, a lipgloss, a lip pencil, a nail varnish, a nail care product or a productfor temporary tattooing of body skin.

Even more particularly, the composition according to the invention hasan advantageous application in the care and the cosmetic treatment, inparticular the protection, of the hair, in particular weakened and/ordamaged hair, for example hair weakened and/or damaged by chemical ormechanical treatments; use may in particular be made of the compoundsaccording to the invention in post-treatment, after a hair dyeing,bleaching or straightening step.

A subject of the invention is therefore a method for cosmeticallytreating, in particular for making up, caring for, cleansing, dyeing orshaping keratin materials, in particular the skin of the body or of theface, the lips, the nails, the hair and/or the eyelashes, comprising theapplication of a cosmetic composition comprising at least one compoundaccording to the invention to said materials.

Preferably, it is a cosmetic treatment method for conditioning the hair,in particular for giving it body and/or liveliness, or improving thedisentangling, smoothing, combability, repair and manageability of thehead of hair. It may be a method for repairing and/or protecting damagedor weakened hair.

In one particular embodiment of the treatment method, the compositionaccording to the invention can be applied all at once, or preferably inseveral applications (multi-application).

Thus, it is possible to apply a composition comprising the compoundsaccording to the invention, in an amount, for example, of from 0.05% to1%, in particular 0.1% to 0.5% by weight, to the hair a first time, toleave it in for 2 to 20, in particular 10, minutes, optionally whileheating at a temperature below 65° C., or else with a smoothing iron ora crimping iron, for example for a few seconds, and then, optionally, todry the hair before applying the composition a second time, and to againleave-in for 2 to 20, in particular 10, minutes, before optionallyheating at a temperature below 65° C., or else with a smoothing iron ora crimping iron, for example for a few seconds, and then to dry or allowto dry. It is possible to carry out a third application of thecomposition. This multi-application of the composition can in particularmake it possible to improve the penetration of the compounds inside thehair, and therefore to improve the repair of the hair in situ.

In another embodiment of the method according to the invention, it ispossible to apply to the hair a composition comprising the compoundsaccording to the invention, in an amount, for example, of from 0.05% to15%, in particular 0.5% to 10% by weight, preferably 1% to 8% by weight,to leave-in for 15 to 45, in particular 30, minutes, preferably whileheating at a temperature below 65° C., or else with a smoothing iron ora crimping iron, for example for a few seconds, and then to rinse outand dry or leave to dry.

The invention is illustrated in greater detail in the followingexemplary embodiments.

EXAMPLE 1 Preparation of(5R,6S,7R,8S)-5,6,7,8-tetrahydroxy-23-[(6-methyl-4-oxo-1,4-dihydropyrimidin-2-yl)amino]-4,9,14,23-tetraoxo-13-oxa-3,10,15,22-tetraazatricos-1-yl[6-({[(6-methyl-4-oxo-1,4-dihydropyrimidin-2-yl)-amino]carbonyl}amino)hexyl]carbamate

1 g of1-(6-isocyanatohexyl)-3-(6-methyl-4-oxo-1,4-dihydropyrimidin-2-yl)urea(3.4 mmol), prepared beforehand according to the procedure described byMeijer et al., is added to a solution of 0.5 g of(2R,3S,4R,5S)-2,3,4,5-tetrahydroxy-N,N′-bis(2-hydroxyethyl)hexanediamide(1.7 mmol) and 0.5 ml of dibutyltin dilaurate in 50 ml of2-methyltetrahydrofuran. The solution is stirred at reflux for 48 hours.20 ml of ethanol are added and the final product is filtered, and isdried under reduced pressure.

1 g (1.1 mmol) of the compound is obtained in the form of a whitepowder.

¹H NMR (DMSO): δ 1.22-1.39 ppm (m, 8H); 1.40-1.63 ppm (m, 8H); 2.05-2.18ppm (s, 6H); 3.08-3.2 ppm (m, 8H); 3.29-3.38 ppm (m, 8H), 3.39-3.47 ppm(q, 1H), 3.75-3.89 ppm (m, 1H), 4.07-4.19 ppm (d, 1H), 4.3-4.45 ppm (m,1H), 4.61-4.75 ppm (t, 1H), 5.18-5.28 ppm (d, 1H), 5.74-5.86 ppm (s, 2H)(in accordance with the expected structure).

EXAMPLE 2

0.4 g of compound of example 1 is mixed into 4 ml of water, and 1.3 mlof a 32% ammonia solution are added. The mixture is stirred for 10minutes at 25° C. A composition which can be applied to the hair isobtained.

Thus, locks of hair of SA20 type can be immersed in this composition for30 minutes at 65° C. The lock can subsequently be wrung out and combed,and then rinsed and dried in an oven at 60° C. for 30 minutes.

1. A cosmetic composition comprising, in a cosmetically acceptablemedium, at least one compound of formula (I):

wherein: n is 1, 2, 3 or 4; R1, R′1, R2 and R′2, which may be identicalor different, are H, —OH, —NRR′ (wherein R and R′, are independently Hor a linear or branched C1-C12 alkyl radical; or a linear, branchedand/or cyclic, saturated or unsaturated, optionally aromatic, C1-C18carbon group which optionally comprises one or more heteroatoms selectedfrom the group consisting of O, S and N; p and q are, independently ofone another, integers between 1 and 16; X and X′ are, independently ofone another, —O— and or —NH— Z is a multivalent radical selected fromthe group consisting of: (i) a linear or branched, saturated orunsaturated, C1 to C32 carbon radical, optionally interrupted orsubstituted, one or more times, with an optionally aromatic C3-C12(hetero)cycle; or (ii) an optionally aromatic C3-C12 (hetero)cycliccarbon radical, optionally substituted with one or more linear orbranched, saturated or unsaturated, C1 to C32 carbon-based radicals;wherein Z is optionally: substituted with 1 to 12 groups selected fromthe group consisting of —OH, —SO₃R, —OSO₃R, —SO₃H, —OSO₃H, —COOH, —COOR,—CONRR′ and —N⁺RR′R″, wherein R, R′ and R″ are independently C1-C12alkyl, in particular methyl; and/or interrupted with 1 to 12 groupsselected from the group consisting of: —S—, —NH— (or ═NH), —O—, —C(O)—,—SO₂—,

wherein R′ and R″, which may be identical or different, are a hydrogenatom or a linear, branched and/or cyclic, saturated or unsaturated,carbon radical containing 1 to 22 carbon atoms, (i) optionallysubstituted with one or more groups selected from the group consistingof —SO₃R₁, —OSO₃R₁, —COOR₁, —Si(OR₁)₃, —N⁺R₁R₂R₃ or —NR₁R₂, in which R₁,R₂ and R₃, independently of one another, are H or C1-C22, alkyl, andoptionally interrupted with at least one selected from the groupconsisting of —NH, —O— and —C(O)— the following trivalent groups:

wherein R′ is defined above the trivalent groups are present at thejunction of the radicals; with the proviso that the Z radical comprisesat least one substitution group selected from the group consisting of:—OH, —COOH, —COOR, CONRR′ and —N⁺RR′R″; or at least one interruptiongroup selected from the group consisting of: —S—, —NH— (or ═NH),


2. The cosmetic composition according to claim 1, wherein the compoundof formula (I) comprises at least one selected from the group consistingof: X and X′ are 0; R1 and/or R′1 are H; and R2 and/or R′2 are H, CH₃,C₇H₁₅, C₁₃H₂₇ or aryl.
 3. The cosmetic composition according to claim 1,wherein the substitution group is selected from the group consisting of—COOH, —COOMe and —CONRR′ (wherein R and R′ are C1-C6 alkyl; and/or theinterruption group is selected from the group consisting of —S—, —NH—,—N⁺(R′)(R″)— and trivalent N.
 4. The cosmetic composition according toclaim 1, wherein the Z radical is a linear or branched, saturated orunsaturated, C1 to C32 divalent or trivalent hydrocarbon radicalcomprising at least one unit of the type —NR′—; —N⁺R′R″—, —NR′C(O)—,—NR′C(O)NR″—, or —NR′C(O)O—, wherein R′ and R″ are hydrogen, or a C3-C7cycloalkyl, benzyl, phenyl or linear or branched C1-C22 alkyl chain. 5.The cosmetic composition according to claim 1, wherein n=1 and thedivalent Z radical is selected from the group consisting of:


6. The cosmetic composition according to claim 1 wherein n is 2 and Z isa trivalent radical selected from the group consisting of:

wherein p is 1 to
 6. 7. The cosmetic composition according to claim 1,wherein the compound of formula (I) is selected from the groupconsisting of the following compounds:


8. The cosmetic composition according to claim 1, wherein a content ofthe compound of formula (I) is from 0.001% to 15% by weight, relative tothe total weight of the composition.
 9. A cosmetic composition for haircare, cleansing of hair, styling of hair, hair form retention, hairshaping or hair dyeing comprising the composition according to claim 1.10. A method for cosmetically treating keratin materials, whichcomprises applying a cosmetic composition as defined in claim 1 thekeratin materials.
 11. The method according to claim 10, wherein thekeratin materials are hair.
 12. The method according to claim 11,wherein the cosmetic treatment is for conditioning the hair, giving atleast one of body and liveliness to the hair, or improvingdisentangling, smoothing, combability, repair and manageability of thehair.
 13. The method according to claim 11, wherein the treatment is forat least one of repairing and protecting damaged or weakened hair.
 14. Acompound of formula (I):

wherein: n is 1, 2, 3 or 4; R1, R′1, R2 and R′2, which may be identicalor different, are H, —OH, —NRR′ (wherein R and R′, are independently Hor a linear or branched C1-C12 alkyl radical; or a linear, branchedand/or cyclic, saturated or unsaturated, optionally aromatic, C1-C18carbon group which optionally comprises one or more heteroatoms selectedfrom the group consisting of O, S and N; p and q are, independently ofone another, integers between 1 and 16; X and X′ are, independently ofone another, —O— and or —NH— Z is a multivalent radical selected fromthe group consisting of: (i) a linear or branched, saturated orunsaturated, C1 to C32 carbon radical, optionally interrupted orsubstituted, one or more times, with an optionally aromatic C3-C12(hetero)cycle; or (ii) an optionally aromatic C3-C12 (hetero)cycliccarbon radical, optionally substituted with one or more linear orbranched, saturated or unsaturated, C1 to C32 carbon-based radicals;wherein Z is optionally: substituted with 1 to 12 groups selected fromthe group consisting of —OH, —SO₃R, —OSO₃R, —SO₃H, —OSO₃H, —COOH, —COOR,—CONRR′ and —N⁺RR′R″, wherein R, R′ and R″ are independently C1-C12alkyl, in particular methyl; and/or interrupted with 1 to 12 groupsselected from the group consisting of: —S—, —NH— (or ═NH), —O—, —C(O)—,—SO₂—,

wherein R′ and R″, which may be identical or different, are a hydrogenatom or a linear, branched and/or cyclic, saturated or unsaturated,carbon radical containing 1 to 22 carbon atoms, (i) optionallysubstituted with one or more groups selected from the group consistingof —SO₃R₁, —OSO₃R₁, —COOR₁, —Si(OR₁)₃, —N⁺R₁R₂R₃ or —NR₁R₂, in which R₁,R₂ and R₃, independently of one another, are H or C1-C22, alkyl, andoptionally interrupted with at least one selected from the groupconsisting of —NH, —O— and —C(O)—; the following trivalent groups:

wherein R′ is defined above the trivalent groups are present at thejunction of the radicals; with the proviso that the Z radical comprisesat least one substitution group selected from the group consisting of:—OH, —COOH, —COOR, CONRR′ and —N⁺RR′R″; or at least one interruptiongroup selected from the group consisting of: —S—, —NH— (or ═NH),